#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024421.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024421
loop_
_publ_author_name
'Min Jiang'
'Min Shi'
_publ_section_title
;
Reactions of Monoaryl-Substituted Methylenecyclobutanes and
Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt),
1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2516
_journal_page_last               2520
_journal_paper_doi               10.1021/jo9000299
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C17 H14 Br N3 O2'
_chemical_formula_weight         372.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.417(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8939(10)
_cell_length_b                   10.3365(18)
_cell_length_c                   26.251(5)
_cell_measurement_reflns_used    1433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.726
_cell_measurement_theta_min      5.016
_cell_volume                     1599.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1217
_diffrn_reflns_av_sigmaI/netI    0.1300
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9101
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7563
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                1523
_reflns_number_total             3469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9000299_si_001.cif
_cod_data_source_block           cd27564
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 1.17142(10) 0.58195(5) 0.11955(3) 0.0922(3) Uani 1 1 d . . .
O1 O 0.7873(4) -0.0456(3) 0.11312(10) 0.0478(8) Uani 1 1 d . . .
O2 O 0.5246(6) 0.0928(3) 0.21799(14) 0.0818(11) Uani 1 1 d . . .
N1 N 0.5840(6) -0.0602(3) 0.08722(13) 0.0465(9) Uani 1 1 d . . .
N2 N 0.4235(6) 0.0331(4) 0.08837(14) 0.0540(10) Uani 1 1 d . . .
N3 N 0.2674(6) 0.0005(4) 0.05546(15) 0.0562(10) Uani 1 1 d . . .
C1 C 0.7564(7) -0.0461(4) 0.16789(16) 0.0472(11) Uani 1 1 d . . .
C2 C 0.6337(8) -0.1644(5) 0.18965(17) 0.0617(13) Uani 1 1 d . . .
H2A H 0.4939 -0.1435 0.2071 0.074 Uiso 1 1 calc R . .
H2B H 0.6098 -0.2331 0.1650 0.074 Uiso 1 1 calc R . .
C3 C 0.8326(8) -0.1878(5) 0.2252(2) 0.0746(15) Uani 1 1 d . . .
H3A H 0.8897 -0.2758 0.2243 0.089 Uiso 1 1 calc R . .
H3B H 0.8057 -0.1602 0.2600 0.089 Uiso 1 1 calc R . .
C4 C 0.9755(8) -0.0915(4) 0.19414(18) 0.0600(13) Uani 1 1 d . . .
H4A H 1.0490 -0.0254 0.2146 0.072 Uiso 1 1 calc R . .
H4B H 1.0825 -0.1324 0.1713 0.072 Uiso 1 1 calc R . .
C5 C 0.6758(7) 0.0856(4) 0.18646(16) 0.0514(11) Uani 1 1 d . . .
C6 C 0.7958(6) 0.2041(4) 0.16804(15) 0.0455(10) Uani 1 1 d . . .
C7 C 0.7050(8) 0.3261(5) 0.17896(17) 0.0587(12) Uani 1 1 d . . .
H7 H 0.5682 0.3313 0.1963 0.070 Uiso 1 1 calc R . .
C8 C 0.8119(8) 0.4382(4) 0.16484(19) 0.0629(13) Uani 1 1 d . . .
H8 H 0.7488 0.5183 0.1724 0.075 Uiso 1 1 calc R . .
C9 C 1.0135(8) 0.4299(4) 0.13932(17) 0.0547(12) Uani 1 1 d . . .
C10 C 1.1092(8) 0.3127(5) 0.12795(16) 0.0537(11) Uani 1 1 d . . .
H10 H 1.2478 0.3091 0.1113 0.064 Uiso 1 1 calc R . .
C11 C 0.9979(7) 0.1991(4) 0.14150(15) 0.0505(11) Uani 1 1 d . . .
H11 H 1.0595 0.1194 0.1327 0.061 Uiso 1 1 calc R . .
C12 C 0.5382(7) -0.1529(4) 0.05201(14) 0.0394(10) Uani 1 1 d . . .
C13 C 0.3338(7) -0.1130(4) 0.03193(16) 0.0466(11) Uani 1 1 d . . .
C14 C 0.2271(8) -0.1843(5) -0.00738(16) 0.0580(13) Uani 1 1 d . . .
H14 H 0.0881 -0.1600 -0.0213 0.070 Uiso 1 1 calc R . .
C15 C 0.3425(9) -0.2920(5) -0.02363(18) 0.0670(14) Uani 1 1 d . . .
H15 H 0.2798 -0.3416 -0.0497 0.080 Uiso 1 1 calc R . .
C16 C 0.5483(9) -0.3296(4) -0.00267(18) 0.0609(13) Uani 1 1 d . . .
H16 H 0.6175 -0.4040 -0.0151 0.073 Uiso 1 1 calc R . .
C17 C 0.6541(8) -0.2623(4) 0.03544(16) 0.0523(11) Uani 1 1 d . . .
H17 H 0.7929 -0.2876 0.0493 0.063 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C1 111.9(3) . . ?
N2 N1 C12 112.5(3) . . ?
N2 N1 O1 121.1(3) . . ?
C12 N1 O1 125.4(3) . . ?
N3 N2 N1 107.0(3) . . ?
N2 N3 C13 108.4(3) . . ?
O1 C1 C5 110.8(3) . . ?
O1 C1 C4 109.6(3) . . ?
C5 C1 C4 113.2(3) . . ?
O1 C1 C2 115.8(3) . . ?
C5 C1 C2 116.4(4) . . ?
C4 C1 C2 89.2(3) . . ?
C3 C2 C1 89.5(3) . . ?
C3 C2 H2A 113.7 . . ?
C1 C2 H2A 113.7 . . ?
C3 C2 H2B 113.7 . . ?
C1 C2 H2B 113.7 . . ?
H2A C2 H2B 111.0 . . ?
C2 C3 C4 89.7(3) . . ?
C2 C3 H3A 113.7 . . ?
C4 C3 H3A 113.7 . . ?
C2 C3 H3B 113.7 . . ?
C4 C3 H3B 113.7 . . ?
H3A C3 H3B 110.9 . . ?
C1 C4 C3 88.5(3) . . ?
C1 C4 H4A 113.9 . . ?
C3 C4 H4A 113.9 . . ?
C1 C4 H4B 113.9 . . ?
C3 C4 H4B 113.9 . . ?
H4A C4 H4B 111.1 . . ?
O2 C5 C6 121.2(4) . . ?
O2 C5 C1 120.1(4) . . ?
C6 C5 C1 118.6(4) . . ?
C11 C6 C7 117.9(4) . . ?
C11 C6 C5 122.8(4) . . ?
C7 C6 C5 119.3(4) . . ?
C8 C7 C6 121.9(4) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 118.7(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 Br 117.9(4) . . ?
C8 C9 Br 120.6(3) . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 120.3(4) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N1 C12 C13 102.6(4) . . ?
N1 C12 C17 133.7(4) . . ?
C13 C12 C17 123.6(4) . . ?
C12 C13 N3 109.4(4) . . ?
C12 C13 C14 120.6(4) . . ?
N3 C13 C14 130.0(4) . . ?
C15 C14 C13 115.5(4) . . ?
C15 C14 H14 122.2 . . ?
C13 C14 H14 122.2 . . ?
C14 C15 C16 122.6(4) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 122.8(4) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 C17 C12 114.8(4) . . ?
C16 C17 H17 122.6 . . ?
C12 C17 H17 122.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C9 1.901(4) . ?
O1 N1 1.382(4) . ?
O1 C1 1.451(5) . ?
O2 C5 1.223(5) . ?
N1 N2 1.351(4) . ?
N1 C12 1.357(5) . ?
N2 N3 1.302(5) . ?
N3 C13 1.384(5) . ?
C1 C5 1.524(6) . ?
C1 C4 1.532(6) . ?
C1 C2 1.533(6) . ?
C2 C3 1.513(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.541(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.496(6) . ?
C6 C11 1.385(5) . ?
C6 C7 1.401(6) . ?
C7 C8 1.371(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(6) . ?
C10 C11 1.393(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 C17 1.393(5) . ?
C13 C14 1.412(6) . ?
C14 C15 1.374(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 N2 67.5(4) . . . . ?
C1 O1 N1 C12 -124.7(4) . . . . ?
C12 N1 N2 N3 2.3(4) . . . . ?
O1 N1 N2 N3 171.5(3) . . . . ?
N1 N2 N3 C13 -2.0(4) . . . . ?
N1 O1 C1 C5 -80.1(4) . . . . ?
N1 O1 C1 C4 154.3(3) . . . . ?
N1 O1 C1 C2 55.3(4) . . . . ?
O1 C1 C2 C3 124.8(4) . . . . ?
C5 C1 C2 C3 -102.3(4) . . . . ?
C4 C1 C2 C3 13.3(4) . . . . ?
C1 C2 C3 C4 -13.2(4) . . . . ?
O1 C1 C4 C3 -130.3(4) . . . . ?
C5 C1 C4 C3 105.5(4) . . . . ?
C2 C1 C4 C3 -13.1(4) . . . . ?
C2 C3 C4 C1 13.2(4) . . . . ?
O1 C1 C5 O2 136.8(4) . . . . ?
C4 C1 C5 O2 -99.6(5) . . . . ?
C2 C1 C5 O2 1.7(6) . . . . ?
O1 C1 C5 C6 -47.3(5) . . . . ?
C4 C1 C5 C6 76.3(5) . . . . ?
C2 C1 C5 C6 177.6(4) . . . . ?
O2 C5 C6 C11 165.3(4) . . . . ?
C1 C5 C6 C11 -10.5(6) . . . . ?
O2 C5 C6 C7 -13.0(6) . . . . ?
C1 C5 C6 C7 171.2(4) . . . . ?
C11 C6 C7 C8 -1.0(6) . . . . ?
C5 C6 C7 C8 177.4(4) . . . . ?
C6 C7 C8 C9 0.0(7) . . . . ?
C7 C8 C9 C10 -0.2(7) . . . . ?
C7 C8 C9 Br -179.2(3) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
Br C9 C10 C11 -179.5(3) . . . . ?
C7 C6 C11 C10 2.2(6) . . . . ?
C5 C6 C11 C10 -176.1(4) . . . . ?
C9 C10 C11 C6 -2.5(6) . . . . ?
N2 N1 C12 C13 -1.5(4) . . . . ?
O1 N1 C12 C13 -170.2(3) . . . . ?
N2 N1 C12 C17 176.7(4) . . . . ?
O1 N1 C12 C17 8.0(7) . . . . ?
N1 C12 C13 N3 0.3(4) . . . . ?
C17 C12 C13 N3 -178.2(4) . . . . ?
N1 C12 C13 C14 179.1(4) . . . . ?
C17 C12 C13 C14 0.7(6) . . . . ?
N2 N3 C13 C12 1.1(5) . . . . ?
N2 N3 C13 C14 -177.6(4) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
N3 C13 C14 C15 177.9(4) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C12 0.4(7) . . . . ?
N1 C12 C17 C16 -178.4(4) . . . . ?
C13 C12 C17 C16 -0.5(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658920
